EP 1783130 A4 20081224 - METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANECARBOXYLATE COMPOUND
Title (en)
METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANECARBOXYLATE COMPOUND
Title (de)
VERFAHREN ZUR HERSTELLUNG EINER OPTISCH AKTIVEN CYCLOPROPANCARBOXYLATVERBINDUNG
Title (fr)
PROCÉDÉ SERVANT À PRODUIRE UN COMPOSÉ CYCLOPROPANECARBOXYLATE OPTIQUEMENT ACTIF
Publication
Application
Priority
- JP 2005012530 W 20050630
- JP 2004195254 A 20040701
Abstract (en)
[origin: EP1783130A1] A process for production of an optically active cyclopropanecarboxylate compound represented by the formula (5): wherein R 6 , R 7 , R 8 and R 9 represent a C1-C6 alkyl group or the like and R 10 represents a C1-C6 alkyl group, which comprises reacting an olefin represented by the formula (3): wherein R 6 , R 7 , R 8 and R 9 are as described above, with a diazoacetic acid ester represented by the formula (4): €ƒ€ƒ€ƒ€ƒ€ƒ€ƒ€ƒ€ƒN 2 CHCO 2 R 10 €ƒ€ƒ€ƒ€ƒ€ƒ(4) wherein R 10 is as described above, in the presence of an asymmetric copper complex obtained by mixing (A) at least one monovalent or divalent copper compound, (B) at least one optically active bisoxazoline compound represented by the formula (1): wherein R 1 and R 2 represent a C1-C6 alkyl group or the like; R 3 represents a tert-butyl group or the like; and R 4 and R 5 are the same and represent C1-C3 alkyl groups or the like, and (C) at least one boron compound represented by the formula (2): wherein A represents a trityl group or the like, X represents a fluorine atom or the like, and n represents an integer of 1 to 5.
IPC 8 full level
C07F 5/02 (2006.01); B01J 31/18 (2006.01); C07C 67/347 (2006.01); C07C 69/757 (2006.01)
CPC (source: EP KR US)
B01J 31/1815 (2013.01 - EP US); C07C 67/347 (2013.01 - EP KR US); C07C 69/003 (2013.01 - KR); C07F 1/08 (2013.01 - KR); C07F 5/02 (2013.01 - KR); C07F 5/027 (2013.01 - EP US); B01J 2231/325 (2013.01 - EP US); B01J 2531/16 (2013.01 - EP US)
Citation (search report)
- [E] EP 1593674 A1 20051109 - SUMITOMO CHEMICAL CO [JP] & WO 2004069815 A1 20040819 - SUMITOMO CHEMICAL CO [JP], et al
- [A] JP 2003012675 A 20030115 - SUMITOMO CHEMICAL CO
- [A] DIAZ-REQUEJO M ET AL: "Kinetics of the BpCu-Catalyzed Carbene Transfer Reaction. (Bp=Dihydridobis(1-pyrazolyl) borate).Is a 14-Electron Species the Real Catalyst for the General Copper-Mediated Olefin Cyclopropanation?", ORGANOMETALLICS, vol. 18, no. 14, 5 July 1999 (1999-07-05), pages 2601 - 2609, XP002992017, ISSN: 0276-7333
- [A] LLEWELLYN D B ET AL: "A Novel Example of Chiral Counteranion Induced Enantioselective Metal Catalysis: The Importance of Ion-Pairing in Copper-Catalyzed Olefin Aziridination and Cyclopropanation", ORGANIC LETTERS, vol. 2, no. 26, 28 December 2000 (2000-12-28), pages 4165 - 4168, XP007906345, ISSN: 1523-7060
- See references of WO 2006004178A1
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR
DOCDB simple family (publication)
EP 1783130 A1 20070509; EP 1783130 A4 20081224; EP 1783130 B1 20091230; AT E453651 T1 20100115; CN 100545166 C 20090930; CN 1968958 A 20070523; DE 602005018656 D1 20100211; ES 2336465 T3 20100413; IL 179704 A0 20070515; IL 179704 A 20100616; JP 2006045194 A 20060216; JP 5002916 B2 20120815; KR 101156372 B1 20120613; KR 20070032032 A 20070320; US 2009048450 A1 20090219; US 7671210 B2 20100302; WO 2006004178 A1 20060112; ZA 200700027 B 20080528
DOCDB simple family (application)
EP 05758177 A 20050630; AT 05758177 T 20050630; CN 200580019479 A 20050630; DE 602005018656 T 20050630; ES 05758177 T 20050630; IL 17970406 A 20061129; JP 2005012530 W 20050630; JP 2005173304 A 20050614; KR 20077002179 A 20050630; US 63080305 A 20050630; ZA 200700027 A 20050630